Winter Haven Homes with Boatable Water Water Frontage

Winter Haven Homes with Boatable Water Water Frontage

Winter Haven, located in Polk County, Florida, is a charming city known for its beautiful lakes and boatable water frontage. Situated in the heart of the state, Winter Haven offers residents a perfect blend of natural beauty and modern amenities.

With its true boatable water frontage, Winter Haven is a paradise for water enthusiasts. The city is home to over 50 lakes, including the famous Chain of Lakes, which connects 16 different lakes through a series of canals. Whether you enjoy fishing, boating, or simply relaxing by the water, Winter Haven provides endless opportunities for outdoor recreation.

In addition to its stunning lakes, Winter Haven boasts a vibrant downtown area filled with shops, restaurants, and entertainment venues. The city is also home to the renowned Legoland Florida Resort, a popular destination for families and Lego enthusiasts alike.

When it comes to real estate, Winter Haven offers a wide range of options. From cozy waterfront cottages to spacious lakefront estates, there is a home to suit every taste and budget. Whether you're looking for a permanent residence or a vacation getaway, Winter Haven's homes with boatable water frontage provide a unique opportunity to enjoy the city's natural beauty.

With its picturesque lakes, thriving downtown, and diverse real estate options, Winter Haven is a city that truly has it all. Whether you're a water lover, nature enthusiast, or simply seeking a peaceful community to call home, Winter Haven is the perfect place to settle down and enjoy the best that Florida has to offer.

Newest Winter Haven Homes with Boatable Water Water Frontage

$115,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven
$309,900
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven
$409,900
4 Beds ⋅ 3 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Located in one of Southeast Winter Haven's most desirable neighborhoods, just minutes from the Chain of Lakes and Lake Summit boat ramp, this beautifully updated 4-bedroom, 3-bath pool home offers nearly 2,500 square feet of living space with **no HOA**. Designed with flexibility in mind, the home features two spacious primary suites, multiple living areas, and a beautifully remodeled kitchen with quartz countertops, soft-close cabinetry, stainless steel appliances, and a workstation sink. Step outside to the screened lanai overlooking the private pool and enjoy the fully fenced backyard - perfect for entertaining, pets, and everyday living. Major updates include a NEW ROOF (2019), HVAC (2019), HOT WATER HEATER (2019), primary bathroom remodel (2019), kitchen remodel (2021), pool heater (2022), pool pump (2024), front and backyard irrigation system (2024), and guest bathroom remodel (2025). Offering quality updates, generous living space, and an exceptional location! Schedule your private showing today!

144 Beverly Dr, Winter Haven
$369,900
3 Beds ⋅ 3 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
ARE YOU AN AIRCRAFT OWNER, PILOT, FLYING ENTHUSIAST AND/OR LOOKING FOR ACCESS TO THE CHAIN OF LAKES? Relax and enjoy life in this attractive 2383 SF 3BR/2.5 Bath home with study located in Hartridge Hills, a gated community with boat ramp and dock on Lake Hartridge, adjacent to the Winter Haven airport and near Jack Brown Seaplane Base! The community features CUSTOM EXECUTIVE STYLE homes! When built, this amazing home won the following parade of Homes Awards: Home of the Year; Best Kitchen; Best Master Bath; Best Exterior; Best Overall Quality; and, Best Floor Plan! The home features an open floor plan with split bedrooms, crown molding, volume ceilings, interior laundry room and attractive tile flooring. The kitchen overlooks the dining area and offers granite countertops, wood cabinetry, stainless steel appliances and pantry closet. The primary suite has sliding glass doors leading to the covered lanai, two walk-in closets and en suite bathroom with separate vanities, garden tub, walk around shower and a water closet. Most recent updates include: new landscaping May 2026; new refrigerator June 2025; installation of irrigation well 2025; repainting interior walls, trim and doors 2022; and installation of New 30 year Architectural Shingle Roof April 2022. The Community Offers a BOAT RAMP & DOCK on LAKE HARTRIDGE providing residents access to the CHAIN OF LAKES! HOA fee maintains streets, common areas, lights, gate, boat ramp & dock and mowing and fertilization of yards!! Centrally located with easy access to shopping, restaurants, medical facilities and surrounding towns.

220 Hartridge Hills Dr, Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates Add SubDv. ⋅ 33881 Zip Code
Welcome home to this beautifully maintained residence in the highly sought-after Lake-n-Golf Estates, where comfort, convenience, and an active lifestyle come together. From the moment you arrive, you'll appreciate the attractive epoxy-coated driveway and the inviting front sitting area, creating the perfect private retreat to enjoy your morning coffee or unwind with a good book. Step inside to a bright, vibrant interior featuring luxury vinyl plank flooring installed just a few months ago, offering a fresh, modern feel throughout the home. A brand new roof, less than one year old, provides added peace of mind for years to come. Outside, you'll also find a convenient storage shed, offering plenty of space for tools, hobbies, or seasonal items. Lake-n-Golf Estates is a resident-owned 55+ community known for its welcoming atmosphere and outstanding amenities, including a golf course, heated community pool, clubhouse, shuffleboard courts, and a full calendar of social activities. Conveniently located near shopping, dining, medical facilities, and Winter Haven's beautiful Chain of Lakes, this home offers the perfect blend of relaxation and everyday convenience. Come experience all that this wonderful home and community have to offer.

6666 Briarhill Drive Ne, Winter Haven
$449,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 2 South SubDv. ⋅ 33884 Zip Code
WELCOME to the lifestyle you've been dreaming of in the premier 55+ community of Lake Ashton! This Stunning Designer residence offers the perfect blend of elegance, comfort, and resort-style living with 3 spacious bedrooms, 2 beautifully appointed baths, plus a private den/office in a desirable split-bedroom floor plan. The heart of the home is the spectacular open-concept kitchen, featuring upgraded all-wood raised-panel cabinetry, gleaming granite countertops, stainless steel appliances, abundant storage, and a large breakfast bar overlooking the expansive living and dining areas. Gorgeous tile flooring flows throughout the main living spaces, while plush carpeting adds warmth and comfort to the bedrooms. Natural light fills every room through an abundance of windows, creating a bright and inviting atmosphere. Step through the sliding glass doors onto the screened veranda, where you can relax with your morning coffee or evening cocktail while enjoying peaceful pond views and Florida's beautiful sunsets. The luxurious owner's suite is a private retreat featuring an incredible spa-inspired bath with dual granite vanities, upgraded wood cabinetry, and a spectacular walk-through fully tiled shower designed for both beauty and convenience. Enjoy the pocket doors throughout the house. This house has so many Designer Upgrades, its difficult to list all of them. Life at Lake Ashton is second to none, offering two private golf courses, three pristine natural lakes, two magnificent clubhouses, indoor and outdoor resort-style swimming pools (including a relaxing hot tub), two state-of-the-art fitness centers, racquetball, basketball, tennis, pickleball, scenic walking trails winding throughout the golf course, and the convenience of a golf cart-friendly community. Enjoy dining at the restaurant overlooking the golf course, meet friends for endless social activities and entertainment, and experience the vibrant, active lifestyle you've always imagined. This home has solar panels that will save on your electric bills for years to come. Don't miss this exceptional opportunity to own one of Lake Ashton's most BEAUTIFUL DESIGNER HOMES. Schedule your private showing today and be the first to call this extraordinary residence HOME!

1061 Sawgrass Drive, Winter Haven
$320,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Perfectly situated on a premium pond-front homesite in the sought-after 55+ gated community of Traditions at Lake Ruby, this beautifully maintained residence offers the ideal blend of comfort, space, and carefree Florida living. With 3 bedrooms, 2 bathrooms, and 2,109 square feet of thoughtfully designed living space, the open split-bedroom floor plan is perfect for both everyday living and entertaining. From the moment you arrive, the paver driveway, carriage-style lighting, manicured landscaping, and covered entry create impressive curb appeal. Inside, soaring ceilings and solid-surface flooring enhance the bright, open feel of the home. The spacious kitchen overlooks the family room and features 42-inch maple cabinetry with decorative rain-glass accents, Corian countertops, a breakfast bar, closet pantry, and a charming dining nook. Designed for gathering, the expansive family room is framed by triple sliding glass doors that showcase tranquil pond views and seamlessly connect to the oversized Florida room. Whether you're hosting friends or enjoying a quiet morning coffee, this inviting space provides the perfect backdrop, complete with views of the soothing waterfront fountain. The generously sized primary suite is a true retreat, offering its own waterfront sitting area, direct access to the Florida room, dual walk-in closets, and a spacious en-suite bath featuring a comfort-height double vanity, garden tub, seated walk-in shower, linen closet, and private water closet. Two additional bedrooms provide flexibility for guests, hobbies, or a home office, while the interior utility room includes a washer, dryer, and utility sink for added convenience. Additional highlights include a 2021 roof, 2024 HVAC system, 2018 water heater, gutters, security system, and a two-car garage with an additional refrigerator. Life at Traditions at Lake Ruby feels like a year-round vacation. Residents enjoy an impressive collection of resort-style amenities, including a lakefront clubhouse, heated pool and spa, fitness center, ballroom, library, billiards room, craft and meeting rooms, tennis courts, pickleball courts, bocce ball, basketball, shuffleboard, dog park, private dock, boat ramp, and a full calendar of social activities. The HOA provides exceptional value with lawn maintenance, exterior house painting, cable, internet, and full access to community amenities included. Conveniently located near shopping, dining, medical facilities, major highways, and LEGOLAND, this waterfront gem offers the perfect opportunity to enjoy an active, low-maintenance lifestyle in one of Central Florida’s most desirable 55+ communities.

3614 Plymouth Drive, Winter Haven
$469,000
2 Beds ⋅ 3 Baths ⋅ Hendersons Ext Kenilworth Park SubDv. ⋅ 33881 Zip Code
New Lake Life listing, two houses one price. Must see property with no HOA. Chain of lakes property on Lake Mirror with generator and whole house water system. Main house has beautiful kitchen, big living/dining combo. Kitchen has extra-large refrigerator, island, wall tile, and entry to garage. Large living room has fireplace, storage, and muti doors to sunroom. Primary bedroom has walk in closet, ensuite bathroom, and doors to sunroom. Sunroom faces lake has storage and hurricane windows. Laundry room has washer, dryer, and storage. Covered back porch overlooks pineapple garden. Separate cottage comes fully furnished and has full bath, kitchen, pantry and closet. Cottage overlooks banana and avocado trees. Covered dock overlooks lake with a swing for relaxation. Each house has one bedroom. main house has space to build a second bedroom. 23 chain lakes are connected by canals. All information is deemed reliable but not guaranteed. Buyer must verify all information and measurements. No seller financing.

1620 17th Street Nw, Winter Haven
$615,000
4 Beds ⋅ 2 Baths ⋅ Pollard Shores SubDv. ⋅ 33881 Zip Code
Welcome home to this stunning lakefront 4-bedroom, 2-bath retreat on Lake Hamilton featuring a courtyard outside along with lake views from both the sitting areas and the dining rooms inside of the home. The rooms are spacious, ideal for everyday living and remote work. Whether you're hosting, friends, enjoying family meals, or taking in the scenery after a long day. Spending mornings with coffee, enjoy evenings outdoors, or entertain with ease that comes from a deck right where you want to be, overlooking the lake lifestyle. The community is located near daily conveniences, including shopping, dining, and nearby attractions such as Legoland. From the first look at the views to the comfort of this home, this lakefront home is ready to be enjoyed. Don't miss the opportunity to own a home with lake views in multiple living areas and the added benefit of a deck for outdoor relaxation.

1210 W Lake Hamilton Drive, Winter Haven
$109,000
Inwood SubDv. ⋅ 33881 Zip Code
Build your dream home on this beautiful 0.25-acre Lakefront lot located on Lake Blue Dr NW in the established Inwood community of Winter Haven, Polk County. Offering Direct Frontage on scenic Lake Blue, this waterfront parcel presents a rare opportunity to enjoy lakefront living in the heart of Central Florida. Zoned RL-3 Residential, the property is suitable for a single-family residence or modular home. The lot features approximately 10,720 square feet, paved road frontage, electricity available at the street, nearby city water, and private septic service. With direct lake access and beautiful water views, this property is ideal for a custom home, seasonal retreat, or long-term investment. Enjoy the Florida waterfront lifestyle with opportunities for boating, fishing, kayaking, paddleboarding, and relaxing lake views right from your backyard. Located within a designated Opportunity Zone, the property offers additional long-term investment appeal while remaining conveniently situated near major transportation corridors, including Havendale Boulevard (SR 544), US Highway 92, US Highway 17, and Interstate 4, providing excellent connectivity throughout Central Florida. Conveniently located approximately 10 minutes from Downtown Winter Haven, 15 minutes from Auburndale, 20 minutes from Lakeland, 35 minutes from Walt Disney World, 50 minutes from Orlando International Airport (MCO), and approximately 1 hour from Tampa International Airport (TPA). Nearby amenities include Publix, Walgreens, Wawa, Planet Fitness, restaurants, medical facilities, shopping, entertainment, and everyday conveniences. No HOA. Direct lake frontage. Opportunity Zone location. Paved road access. City water nearby. Electricity available. Financing available with as little as 20% down for qualified buyers.

Lake Blue Drive Nw, Winter Haven
$309,900
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT "TRADITIONS OF RUBY LAKE". This home is MOVE IN READY and is situated withing very close proximity to the clubhouse and Lake Ruby!!! NEW ROOF and NEW HOT WATER HEATER both installed in 2023. With nearly (1,820 Sqft.) of heated and cooled space, this OPEN-CONCEPT SPLIT PLAN with SOARING CEILINGS will not disappoint. There is plenty of room for the chef in the family with your OVERSIZED KITCHEN that has an ABUNDANCE of cabinetry and GRANITE COUNTERTOPS! The kitchen also has 2 windows, giving you a pleasant view along with plenty of extra natural light. Just off the kitchen sits the great room leading into 2 bedrooms and another room (11 x 10) that would be perfect for an office, craft room, or out of town guests. You'll love the (21 x 9) BONUS ROOM that has its own AC and gives you so much extra cooled living space. As if this wasn't enough, the bonus room also overlooks a (21 x 9) SCREENED, PAVERED PATIO for outside grilling or just relaxing. The large primary en-suite has a WALK-IN-SHOWER WITH BUILT-IN BENCH and GLASS SLIDERS, DUAL SINKS, and OVERSIZED WALK-IN-CLOSET. You have direct access to the bonus room from the primary bedroom. Cleaning is a breeze in this home featuring NO CARPET!!! The clubhouse is beautiful and boasts amazing views beyond the pool of 2 lakes (Ruby and Bess). The clubhouse also features an oversized pool and spa, dock, boat ramp, boat slips, tennis courts, pickle ball, basketball, shuffleboard, ball room, billiards, library, craft room, fitness center, dog park and much more! Golf carts are allowed in the community for ease of navigating. Traditions is centrally located in close proximity to medical, shopping, restaurants, 2 major international airports (Tampa/Orlando) and the up and coming airline Avelo in Lakeland, FL. LEGOLAND, FL is just minutes away!

4130 Bedford Avenue, Winter Haven
$1,195,000
5 Beds ⋅ 6 Baths ⋅ Na SubDv. ⋅ 33881 Zip Code
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

250 Brigham Road Nw, Winter Haven
Start Your Search